Triethylamine → HCID 178472035, compound

HRID 491520Notes

Reaction equation

HRID 491520 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.C[N:18]([CH3:26])[CH:19]=[CH:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C.N[CH:35]([OH:37])C>C1(C)C=CC=CC=1.C1COCC1.O.CN(C=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([I:12])=[CH:7][C:3]=1[C:4]([C:20](=[CH:19][NH:18][CH2:26][CH2:35][OH:37])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:6]

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 522583Acetaldehyde ammoniaHCID 108913672,3-Difluoro-5-iodobenzoic acid

Product 1

HCID 178472035HCID 178472035, compoundYield 85%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

2,3-Difluoro-5-iodobenzoic acid (3.0 g, 10.6 mmol) obtained in Step 1 was dissolved in toluene, thionyl chloride (3.0 ml, 41.1 mmol) and DMF (catalytic amount) were added, and the mixture was heated under reflux for 3 hr. The reaction mixture was concentrated under reduced pressure and THF (15 ml) was added to the residue to allow dissolution. The mixture was added dropwise to a solution of ethyl 3-dimethylaminoacrylate (1.66 g, 11.6 mmol) and triethylamine (1.77 ml, 12.7 mmol) in THF (10 ml) and the mixture was stirred with heating at 500C for 2.5 hr. After allowing to cool, the reaction mixture was filtered and washed with THF (10 ml). Aminoethanol (0.77 ml, 12.7 mmol) was added to the filtrate, and the mixture was stirred with heating at 40° C. for 1 hr. After allowing to cool, water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1) to give the object product (3.8 g, yield 85%) as an E and Z mixed yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated under reduced pressure and THF (15 ml)
  4. additionwas added to the residue
  5. dissolutiondissolution
  6. temperatureto cool
  7. filtrationthe reaction mixture was filtered
  8. washwashed with THF (10 ml)
  9. stirringthe mixture was stirred
  10. temperatureto cool
  11. extractionthe mixture was extracted with ethyl acetate
  12. washThe organic layer was washed with water and saturated brine
  13. dry with materialdried over sodium sulfate
  14. filtrationAfter filtration
  15. concentrationthe filtrate was concentrated under reduced pressure
  16. customthe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-83a1162fd0254bb7b309edec968e8959
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

Loading…